7-Amino triazolopyrimidines for controlling harmful fungi

ABSTRACT

The invention relates to 7-amino triazolopyrimidines of formula (I), in which the substituents have the following meanings: R 1 , R 2  represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, naphthyl; or 5-membered or 6-membered heterocyclyl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom; or 5-membered or 6-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, or R 1  and R 2  can, together with the nitrogen atom, which binds them, form a 5-membered or 6-membered ring containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom; R 3  represents alkyl, alkenyl, alkynyl, cycloalkyl, phenylalkyl and alkyl halide; whereby R 3  and R 2  can be unsubstituted or partially or completely substituted according to the description; X represents halogen, cyano, alkoxy, alkyl halide, phenyl or phenyl that is substituted by R a . The invention also relates to methods and intermediate products for producing said compounds, to agents containing the same, and to their use.

The present invention relates to 7-aminotriazolopyrimidines of theformula I,

where:

-   -   R¹, R² are hydrogen, C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl,        C₂-C₁₀-alkynyl, C₃-C₈-cycloalkyl, phenyl, naphthyl; or        -   5- or 6-membered heterocyclyl containing one to four            nitrogen atoms or one to three nitrogen atoms and one sulfur            or oxygen atom; or        -   5- or 6-membered heteroaryl containing one to four nitrogen            atoms or one to three nitrogen atoms and one sulfur or            oxygen atom,        -   where R¹ and R², independently of one another, may, if they            are not hydrogen, be partially or fully halogenated and/or            may carry one to three radicals from the group R^(a)    -   R^(a) is cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,        C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl, C₃-C₆-alkynyloxy        and unhalogenated or halogenated oxy-C₁-C₄-alkyleneoxy, or        -   R¹ and R² together with the linking nitrogen atom may form a            5- or 6-membered ring which contains one to four nitrogen            atoms or one to three nitrogen atoms and one sulfur or            oxygen atom and which may be substituted by one to three            radicals from the group R^(a);    -   R³ is C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl-,        C₃-C₈-cycloalkyl, phenyl-C₁-C₁₀-alkyl,        -   where R³ may be unsubstituted or partially or fully            halogenated and/or may carry one to three radicals from the            group R^(a), or        -   C₁-C₁₀-haloalkyl which may carry one to three radicals from            the group R^(a);    -   X is halogen, cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, phenyl or        R^(a)-substituted phenyl;        and their salts.

Additionally, the invention relates to processes and intermediates forpreparing the compounds I, and also to compositions and to the use ofthe compounds I for controlling harmful fungi.

6-Aryltriazolopyrimidines are disclosed in WO 98/46608 and EP-A 550 113.6-Benzyltriazolopyrimidines which are specifically substituted byaromatic groups and have pharmaceutical action are known from U.S. Pat.No. 5,231,094 and U.S. Pat. No. 5,387,747. EP-A 141 317-discloses7-aminotriazolopyrimidines which may carry an alkyl radical in the5-position. 6-cycloalkyltriazolopyrimidines having various radicals inthe 5-position are mentioned in EP-A 613 900.

The compounds described in WO 98/46608, EP-A 550 113, EP-A 141 317 andEP-A 613 900 are suitable for use as crop protection agents againstharmful fungi.

However, in many cases their action is unsatisfactory. It is an objectof the present invention to provide compounds having improved activity.

We have found that this object is achieved by the7-aminotriazolopyrimidines of the formula I. Furthermore, we have foundintermediates and processes for preparing the compounds I, and the useof the compounds I and of compositions comprising them for controllingharmful fungi.

The compounds of the formula I differ from the compounds known from theabovementioned publications by the combination of the substituents Xwith the radical R³ on the triazolopyrimidine skeleton.

Compounds of the formula I in which X is halogen are obtained, forexample, from dicarbonyl compounds of the formula II.1, which arecyclized with 3-amino-1,2,4-triazole of the formula III to givehydroxytriazolopyrimidines of the formula IV.1:

This reaction is usually carried out at temperaturs of from 25° C. to210° C., preferably from 120° C. to 180° C., in the presence of a base[cf. EP-A-770615].

Suitable bases are, in general, organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, triisopropylethylamine,tributylamine and N-methylpiperidine and pyridine. Particular preferenceis given to triethylamine and tributylamine.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts, in excess or, if appropriate, assolvent.

The starting materials are generally reacted with one another inequimolar amounts. In terms of yield, it may be advantageous to employan excess of II.1 based on III.

The starting materials-required for preparing the compounds I are knownfrom the literature or can be prepared in accordance with the literaturecited [Heterocycl. 1996, 1031-1047; Tetrahedron Lett. 24 (1966),2661-2668], or they are commercially available.

The hydroxytriazolopyrimidines of the formula IV.1 are then reacted witha halogenating agent to give halotriazolopyrimidines of the formula V.1:

This reaction is usually carried out at temperatures of from 0° C. to150° C., preferably from 80° C. to 125° C., in an inert organic solventor without additional solvent [cf. EP-A-770 615].

Suitable halogenating agents are, preferably, brominating orchlorinating agents, such as, for example, phosphorus oxybromide orphosphorus oxychloride, undiluted or in the presence of a solvent.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene,o-, m- and p-xylene, particularly preferably toluene, o-, m- andp-xylene.

It is also possible to use mixtures of the solvents mentioned.

The halotriazolopyrimidines of the formula V.1 are then reacted with anamine of the formula VI to give 7-aminotriazolopyrimidines of theformula I in which X is halogen:

This reaction is usually carried out at temperatures of from 0° C. to70° C., preferably from 10° C. to 35° C., in an inert organic solvent inthe presence of a base [cf. EP-A-550 113].

Suitable solvents are aromatic hydrocarbons, such as toluene, o-, m- andp-xylene, halogenated hydrocarbons, such as methylene chloride,chloroform and chlorobenzene, and ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal amides, such as lithium amide,sodium amide and potassium amide, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, organometallic compounds, in particular alkali metalalkyls, such as methyllithium, butyllithium and phenyllithium,alkylmagnesium halides, such as methylmagnesium chloride, and alsoalkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxideand dimethoxymagnesium, moreover organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, triisopropylethylamineand N-methylpiperidine, pyridine, substituted pyridines, such ascollidine, lutidine and 4-dimethylaminopyridine, and also bicyclicamines. Particular preference is given to triethylamine, potassiumcarbonate and sodium carbonate.

In general, the bases are employed in catalytic amounts; however, theycan also be used in equimolar amounts, in excess or, if appropriate, assolvent. Alternatively, an excess of the compound VI may serve as base.

The starting materials are generally reacted with one another inequimolar amounts. In terms of yield, it may be advantageous to employan excess of VI based on V.I.

To obtain 7-aminotriazolopyrimidines of the formula I in which X iscyano or C₁-C₄-alkoxy, 7-aminotriazolopyrimidines of the formula I arereacted with a compound of the formula VII:

Here, M is an ammonium, tetraalkylammonium, alkali metal or alkalineearth metal cation and XI is cyano or alkoxy. This reaction is usuallycarried out at temperatures of from 0° C. to 150° C., preferably from20° C. to 75° C., in an inert organic solvent [cf. WO 99/41255].

Suitable solvents are ethers, such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols,such as methanol, ethanol, n-propanol, isopropanol, n-butanol andtert-butanol, and also dimethyl sulfoxide, dimethylformamide anddimethylacetamide, particularly preferably diethyl ether,tetrahydrofuran, methanol and dimethylformamide.

It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another inequimolar amounts. In terms of yield, it may be advantageous to employan excess of VII, based on I.

7-Aminotriazolopyrimidines of the formula I in which X isC₁-C₄-haloalkyl or unsubstituted or R^(a)-substituted phenyl can beobtained from dicarbonyl compounds of the formula II.2, which arecyclized with 3-amino-1,2,4-triazole of the formula III to give7-hydroxytriazolopyrimidines of the formula IV.2:

This reaction is carried out under the same conditions as the conversionof II.1 into IV.1 described above.

The 7-hydroxytriazolopyrimidines of the formula IV.2 are then reactedwith a halogenating agent to give 7-halotriazolopyrimidines of theformula V.2:

This reaction is carried out under the same conditions as the conversionof IV.1 into V.1 described above.

Compound V.2 is then reacted with an amine of the formula VI to givecompounds of the formula I:

This reaction is carried out under the same conditions as the conversionof V.1 into I described above.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separation of the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of colorless orslightly brownish viscous oils which can be purified or freed fromvolatile components under reduced pressure and at moderately elevatedtemperature. If the intermediates and end products are obtained assolids, purification can also be carried out by recrystallization ordigestion.

If individual compounds I are not obtainable by the routes describedabove, they can be prepared by derivatization of other compounds I.

7-Hydroxy- and 7-halotriazolopyrimidines of the formulae IV and V,

where Y is a hydroxyl group or a radical from the group X as set forthin claim 1, Hal is halogen and R³ and X are as defined in claim 1 arenovel.

Particular preference is given to intermediates of the formulae IV andV, in which R³ is C₁-C₁₀-alkyl, in particular CH₃, CH₂-CH₃, (CH₂)₃—CH₃,CH₂—CH(CH₃)₂, CH(CH₃)—CH₂—CH₂—CH₃, C(CH₃)₃, (CH₂)₇—CH₃, CH(CH₃)₂,C₂-C₁₀-alkenyl, in particular CH₂—CH═CH₂, C₃-C₈-cycloalkyl, inparticular cyclopropylmethyl, cyclopentyl or cyclohexyl,phenyl-C₁-C₁₀-alkyl, in particular CH₂-C₆H₅, CH₂-o-Cl—C₆H₄,C₁-C₁₀-haloalkyl, in particular CH₂—CF₃, CH(CH₃)—CF₃ or CH(CF₃)₂, and Xis halogen, in particular chlorine, cyano, C₁-C₄-alkoxy,in particularOCH₃, C₁-C₄-haloalkyl, in particular CF₃, phenyl or R^(a)-substitutedphenyl, in particular phenyl.

In the definitions of the symbols given in the above formulae,collective terms were used which generally represent the followingsubstituents:

-   -   halogen: fluorine, chlorine, bromine and iodine;    -   alkyl: saturated, straight-chain or branched hydrocarbon        radicals having 1 to 4, 6, 8 or 10 carbon atoms, for example        C₁-C₆-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl,        1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,        1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,        1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,        1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,        1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,        2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,        1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,        1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and        1-ethyl-2-methylpropyl;    -   haloalkyl: straight-chain or branched alkyl groups having 1 to        10 carbon atoms (as mentioned above), where the hydrogen atoms        in these groups may be partially, for example one to three        times, or fully replaced by halogen atoms as mentioned above,        for example C₁-C₂-haloalkyl such as chloromethyl, bromomethyl,        dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,        trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,        chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,        1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl and pentafluoroethyl;    -   alkoxy: straight-chain or branched alkyl groups having 1 to 6        carbon atoms (as mentioned above) which are linked to the        skeleton via an oxygen atom (—O—);    -   haloalkoxy: straight-chain or branched haloalkyl groups having 1        to 6 carbon atoms (as mentioned above) which are linked to the        skeleton via an oxygen atom (—O—);    -   alkylthio: straight-chain or branched alkyl groups having 1 to 6        carbon atoms (as mentioned above) which are linked to the        skeleton via a sulfur atom (—S—);    -   alkylamino: a straight-chain or branched alkyl group having 1 to        6 carbon atoms (as mentioned above) which is linked to the        skeleton via an amino group (—NH—);    -   dialkylamino: two straight-chain or branched alkyl groups having        in each case 1 to 6 carbon atoms (as mentioned above) which are        independent of each other and which are linked to the skeleton        via a nitrogen atom;    -   alkenyl: unsaturated, straight-chain or branched hydrocarbon        radicals having 2 to 6 or 10 carbon atoms and a double bond in        any position, for example C₂-C₆-alkenyl such as ethenyl,        1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,        3-butenyl, 1-methyl-l-propenyl, 2-methyl-1-propenyl,        1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl,        2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,        2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,        2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,        2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,        1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,        1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,        3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,        2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,        1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,        4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,        3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,        2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,        1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,        1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,        1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,        1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,        2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,        2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,        3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,        l-ethyl-l-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,        2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,        1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,        1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;    -   alkenyloxy: unsaturated, straight-chain or branched hydrocarbon        radicals having 3 to 6 carbon atoms and a double bond in any        position which is not adjacent to the hetero atom (as mentioned        above) which are linked to the skeleton via an oxygen atom        (—O—);    -   alkynyl: straight-chain or branched hydrocarbon groups having 2        to 6 or 10 carbon atoms and a triple bond in any position, for        example C₂-C₆-alkynyl such as ethynyl, 1-propynyl, 2-propynyl,        1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,        1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,        1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,        3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,        1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,        1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,        2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,        3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,        1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,        1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,        3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,        2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;    -   alkynyloxy: unsaturated, straight-chain or branched hydrocarbon        radicals having 3 to 6 carbon atoms and a triple bond in any        position which is not adjacent to the hetero atom (as mentioned        above) which are linked to the skeleton via an oxygen atom        (—O—);    -   cycloalkyl: monocyclic, saturated hydrocarbon groups having 3 to        5, 6 or 8 carbon ring members, for example C₃-C₈-cycloalkyl such        as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl        and cyclooctyl;    -   5- or 6-membered heterocycles (heterocyclyl) containing, in        addition to carbon ring members, one to four nitrogen atoms        and/or one oxygen or sulfur atom or one oxygen and/or sulfur        atom, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl,        2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,        3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,        5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,        5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl,        5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl,        2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,        2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl,        1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl,        1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,        1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,        1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,        2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,        2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,        2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl,        2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,        2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,        2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,        2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,        2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,        2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,        2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,        2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,        2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,        2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,        3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,        3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,        4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,        4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl,        2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,        2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,        3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,        3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,        3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl,        3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,        2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,        3-hexahydropyridazinyl, 4-hexahydropyridazinyl,        2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl,        5-hexahydropyrimidinyl, 2-piperazinyl,        1,3,5-hexahydro-triazin-2-yl and 1,2,4-hexahydrotriazin-3-yl;    -   5-membered heteroaryl, containing one to four nitrogen atoms or        one to three nitrogen atoms and one sulfur or oxygen atom:        heteroaryl groups having 5 ring members which, in addition to        carbon atoms, may contain one to four nitrogen atoms or one to        three nitrogen atoms and one sulfur or oxygen atom as ring        members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,        2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl,        5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl,        3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl,        5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl,        4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,        1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,        1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl        and 1,3,4-triazol-2-yl;    -   6-membered heteroaryl, containing one to three or one to four        nitrogen atoms: heteroaryl groups having 6 ring members which,        in addition to carbon atoms, may contain one to three or one to        four nitrogen atoms as ring members, for example 2-pyridinyl,        3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,        2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,        1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;    -   oxyalkyleneoxy: divalent unbranched chains of 1 to 3 CH₂ groups,        where both valencies are attached to the skeleton via an oxygen        atom, for example OCH₂O, OCH₂CH₂O and OCH₂CH₂CH₂O.

The compounds of the formula I can also be present in the form of theiragriculturally useful salts, the nature of the salt generally beingimmaterial. In general, the salts of those cations and the acid additionsalts of those acids are suitable whose cations and anions,respectively, have no adverse effect on the fungicidal action of thecompounds I.

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium and potassium, of the alkaline earth metals, preferablycalcium and magnesium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium, where, if desired,one to four hydrogen atoms may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di-(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

With respect to the intended use of the 7-aminotriazolopyrimidines ofthe formula I, particular preference is given to the following meaningsof the substituents, in each case on their own or in combination:

Compounds I in which R¹, R² are hydrogen, C₁-C₁₀-alkyl orC₁-C₆-haloalkyl, in particular hydrogen, C₁-C₆-alkyl or C₁-C₄-haloalkyl,particularly preferably hydrogen, 1-methylpropyl, isopropyl or1,1,1-trifluoro-2-propyl, or where

-   -   R¹ and R² together with the linking nitrogen atom form a 5- or        6-membered ring which may contain an oxygen atom and/or may        carry a C₁-C₄-alkyl radical, for example pyrrolidin-1-yl,        pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, piperidin-1-yl or        morpholin-4-yl, where the radicals mentioned may be substituted        by one to three radicals R^(a), in particular by C₁-C₄-alkyl,        such as, for example, methyl or ethyl.

In addition, particular preference is also given to compounds I in whichR¹ is hydrogen, C₁-C₆-alkyl or C₁-C₄-haloalkyl and R² is hydrogen.

Very particular preference is also given to compounds I in which R¹ andR² are hydrogen and R³ is C₃-C₈-cycloalkyl, preferably cyclopropyl,cyclopentyl or cyclohexyl.

Moreover, particular preference is given to compounds I in which R³ isC₁-C₈-alkyl, in particular isopropyl or n-octyl, C₃-C₆-cycloalkyl,particularly preferably cyclopropyl, cyclopentyl or cyclohexyl, orCH₂—C₆H₅.

Particular preference is also given to compounds I in which R³ isC₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl, particularlypreferably cyclopropyl, cyclopropylmethyl, cyclopentyl or cyclohexyl,and X is cyano, C₁-C₄-alkoxy, for example OCH₃, C₁-C₄-haloalkyl, forexample CF₃, or an optionally R^(a)-substituted phenylalkyl, for exampleCH₂—C₆H₅ or CH₂-o-Cl—C₆H₄.

Moreover, particular preference is given to compounds I in which R³ isC₃-C₈-cycloalkyl, in particular C₃-C₆-cycloalkyl, with particularpreference cyclopropyl, cyclopentyl or cyclohexyl, and X is halogen, inparticular chlorine.

Particular preference is likewise given to compounds I in which X ishalogen, such as chlorine or bromine, in particular chlorine.

With respect to their use, particular preference is given to thecompounds I compiled in the tables below. Moreover, the groups mentionedfor a substituent in the tables are, by themselves and independently ofthe combination in which they are mentioned, a particularly preferredembodiment of the substituent in question.

Table 1

Compounds of the formula I in which R³ is CH₃ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 2

Compounds of the formula I in which R³ is CH₂—CH₃ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 3

Compounds of the formula I in which R³ is (CH₂)₃—CH₃ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 4

Compounds of the formula I in which R³ is CH₂—CH(CH₃)₂ and X is Cl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 5

Compounds of the formula I in which R³ is CH(CH₃)—CH₂—CH₂—CH₃ and X isCl and the combination of the radicals R¹ and R² for a compoundcorresponds in each case to one row of Table A

Table 6

Compounds of the formula I in which R³ is C(CH₃)₃ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 7

Compounds of the formula I in which R³ is (CH₂)₇—CH₃ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 8

Compounds of the formula I in which R³ is CH(CH₃)₂ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 9

Compounds of the formula I in which R³ is cyclopentyl and X is Cl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 10

Compounds of the formula I in which R³ is cyclohexyl and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 11

Compounds of the formula I in which R³ is CH₂—C₆H₅ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 12

Compounds of the formula I in which R³ is CH₂-o-Cl—C₆H₄ and X is Cl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 13

Compounds of the formula I in which R³ is (CH₂)₂—CH₃ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 14

Compounds of the formula I in which R³ is CH₂—CH═CH₂ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 15

Compounds of the formula I in which R³ is cyclopropylmethyl and X is Cland the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 16

Compounds of the formula I in which R³ is CH₂—CH₂—CN and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 17

Compounds of the formula I in which R³ is CH₂—CF₃ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 18

Compounds of the formula I in which R³ is CH(CH₃)—CF₃ and X is Cl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 19

Compounds of the formula I in which R³ is CH(CF₃)₂ and X is Cl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 20

Compounds of the formula I in which R³ is CH₃ and X is CF₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 21

Compounds of the formula I in which R³ is CH₂—CH₃ and X is CF₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 22

Compounds of the formula I in which R³ is (CH₂)₃—CH₃ and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 23

Compounds of the formula I in which R³ is CH₂—CH(CH₃)₂ and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 24

Compounds of the formula I in which R³ is CH(CH₃)—CH₂—CH₂—CH₃ and X isCF₃ and the combination of the radicals R¹ and R² for a compoundcorresponds in each case to one row of Table A

Table 25

Compounds of the formula I in which R³ is CH(CH₃)₃ and X is CF₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 26

Compounds of the formula I in which R³ is (CH₂)₇—CH₃ and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 27

Compounds of the formula I in which R³ is CH(CH₃)₂ and X is CF₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 28

Compounds of the formula I in which R³ is cyclopentyl and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 29

Compounds of the formula I in which R³ is cyclohexyl and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 30

Compounds of the formula I in which R³ is CH₂—C₆H₅ and X is CF₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 31

Compounds of the formula I in which R³ is CH₂-p-Cl—C₆H₄ and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 32

Compounds of the formula I in which R³ is (CH₂)₂—CH₃ and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 33

Compounds of the formula I in which R³ is CH₂—CH═CH₂ and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 34

Compounds of the formula I in which R³ is cyclopropylmethyl and X is CF₃and the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 35

Compounds of the formula I in which R³ is CH₂—CH₂—CN and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 36

Compounds of the formula I in which R³ is CH₂—CF₃ and X is CF₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 37

Compounds of the formula I in which R³ is CH(CH₃)—CF₃ and X is CF₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 38

Compounds of the formula I in which R³ is CH(CF₃)₂ and X is CF₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 39

Compounds of the formula I in which R³ is CH₃ and X is phenyl and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 40

Compounds of the formula I in which R³ is CH₂—CH₃ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 41

Compounds of the formula I in which R³ is (CH₂)₃—CH₃ and X is phenyl andthe combination of the radicals. R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 42

Compounds of the formula I in which R³ is CH₂—CH(CH₃)₂ and X is phenyland the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 43

Compounds of the formula I in which R³ is CH(CH₃)—CH₂—CH₂—CH₃ and X isphenyl and the combination of the radicals R¹ and R² for a compoundcorresponds in each case to one row of Table A

Table 44

Compounds of the formula I in which R³ is CH(CH₃)₃ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 45

Compounds of the formula I in which R³ is (CH₂)₇—CH₃ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 46

Compounds of the formula I in which R³ is CH(CH₃)₂ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 47

Compounds of the formula I in which R³ is cyclopentyl and X is phenyland the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 48

Compounds of the formula I in which R³ is cyclohexyl and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 49

Compounds of the formula I in which R³ is CH₂—C₆H₅ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 50

Compounds of the formula I in which R³ is CH₂-p-Cl—C₆H₄ and X is phenyland the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 51

Compounds of the formula I in which R³ is (CH₂)₂—CH₃ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 52

Compounds of the formula I in which R³ is CH₂—CH═CH₂ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 53

Compounds of the formula I in which R³ is cyclopropylmethyl and X isphenyl and the combination of the radicals R¹ and R² for a compoundcorresponds in each case to one row of Table A

Table 54

Compounds of the formula I in which R³ is —CH₂—CH₂—CN and X is phenyland the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 55

Compounds of the formula I in which R³ is CH₂—CF₃ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 56

Compounds of the formula I in which R³ is CH(CH₃)—CF₃ and X is phenyland the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 57

Compounds of the formula I in which R³ is CH(CF₃)₂ and X is phenyl andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 58

Compounds of the formula I in which R³ is CH₃ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 59

Compounds of the formula I in which R³ is CH₂—CH₃ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 60

Compounds of the formula I in which R³ is (CH₂)₃—CH₃ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 61

Compounds of the formula I in which R³ is CH₂—CH(CH₃)₂ and X is CN andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 62

Compounds of the formula I in which R³ is CH(CH₃)—CH₂—CH₂—CH₃ and X isCN and the combination of the radicals R¹ and R² for a compoundcorresponds in each case to one row of Table A

Table 63

Compounds of the formula I in which R³ is CH(CH₃)₃ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 64

Compounds of the formula I in which R³ is (CH₂)₇—CH₃ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 65

Compounds of the formula I in which R³ is CH(CH₃)₂ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 66

Compounds of the formula I in which R³ is cyclopentyl and X is CN andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 67

Compounds of the formula I in which R³ is cyclohexyl and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 68

Compounds of the formula I in which R³ is CH₂—C₆H₅ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 69

Compounds of the formula I in which R³ is CH₂-p-Cl—C₆H₄ and X is CN andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A.

Table 70

Compounds of the formula I in which R³ is (CH₂)₂—CH₃ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 71

Compounds of the formula I in which R³ is CH₂—CH═CH₂ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 72

Compounds of the formula I in which R³ is cyclopropylmethyl and X is CNand the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 73

Compounds of the formula I in which R³ is CH₂—CH₂—CN and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 74

Compounds of the formula I in which R³ is CH₂—CF₃ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 75

Compounds of the formula I in which R³ is CH(CH₃)—CF₃ and X is CN andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 76

Compounds of the formula I in which R³ is CH(CF₃)₂ and X is CN and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 77

Compounds of the formula I in which R³ is CH₃ and X is OCH₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 78

Compounds of the formula I in which R³ is CH₂—CH₃ and X is OCH₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 79

Compounds of the formula I in which R³ is (CH₂)₃—CH₃ and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 80

Compounds of the formula I in which R³ is CH₂—CH(CH₃)₂ and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 81

Compounds of the formula I in which R³ is CH(CH₃)—CH₂—CH₂—CH₃ and X isOCH₃ and the combination of the radicals R¹ and R² for a compoundcorresponds in each case to one row of Table A

Table 82

Compounds of the formula I in which R³ is CH(CH₃)₃ and X is OCH₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 83

Compounds of the formula I in which R³ is (CH₂)₇—CH₃ and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 84

Compounds of the formula I in which R³ is CH(CH₃)₂ and X is OCH₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 85

Compounds of the formula I in which R³ is cyclopentyl and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 86

Compounds of the formula I in which R³ is cyclohexyl and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 87

Compounds of the formula I in which R³ is CH₂—C₆H₅ and X is OCH₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 88

Compounds of the formula I in which R³ is CH₂-p-Cl—C₆H₄ and X is OCH₃and the combination of the radicals R¹ and R² for a compound correspondsin each case to one row of Table A

Table 89

Compounds of the formula I in which R³ is (CH₂)₂—CH₃ and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 90

Compounds of the formula I in which R³ is CH₂—CH═CH₂ and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 91

Compounds of the formula I in which R³ is cyclopropylmethyl and X isOCH₃ and the combination of the radicals R¹ and R² for a compoundcorresponds in each case to one row of Table A

Table 92

Compounds of the formula I in which R³ is CH₂—CH₂—CN and X is OCH₃ andthe combination of the radicals R¹ and R² for a compound corresponds ineach case to one row of Table A

Table 93

Compounds of the formula I in which R³ is CH₂—CF₃ and X is OCH₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A

Table 94

Compounds of the formula I in which R³ is CH(CH₃)—CF₃ and X is OCH₃ andthe combination of the radicals R₁ and R² for a compound corresponds ineach case to one row of Table A

Table 95

Compounds of the formula I in which R³ is CH(CF₃)₂ and X is OCH₃ and thecombination of the radicals R¹ and R² for a compound corresponds in eachcase to one row of Table A TABLE A

No. R¹ R² A-1 H H A-2 CH₂CH₃ H A-3 CH₂CH₃ CH₃ A-4 CH₂CH₃ CH₂CH₃ A-5CH₂CF₃ H A-6 CH₂CF₃ CH₃ A-7 CH₂CF₃ CH₂CH₃ A-8 CH₂CCl₃ H A-9 CH₂CCl₃ CH₃A-10 CH₂CCl₃ CH₂CH₃ A-11 CH₂CH₂CH₃ H A-12 CH₂CH₂CH₃ CH₃ A-13 CH₂CH₂CH₃CH₂CH₃ A-14 CH₂CH₂CH₃ CH₂CH₂CH₃ A-15 CH(CH₃)₂ H A-16 CH(CH₃)₂ CH₃ A-17CH(CH₃)₂ CH₂CH₃ A-18 (R/S) CH(CH₃)—CH₂CH₃ H A-19 (R/S) CH(CH₃)—CH₂CH₃CH₃ A-20 (R/S) CH(CH₃)—CH₂CH₃ CH₂CH₃ A-21 (R) CH(CH₃)—CH₂CH₃ H A-22 (R)CH(CH₃)—CH₂CH₃ CH₃ A-23 (R) CH(CH₃)—CH₂CH₃ CH₂CH₃ A-24 (S)CH(CH₃)—CH₂CH₃ H A-25 (S) CH(CH₃)—CH₂CH₃ CH₃ A-26 (S) CH(CH₃)—CH₂CH₃CH₂CH₃ A-27 (R/S) CH(CH₃)—CH(CH₃)₂ H A-28 (R/S) CH(CH₃)—CH(CH₃)₂ CH₃A-29 (R/S) CH(CH₃)—CH(CH₃)₂ CH₂CH₃ A-30 (R) CH(CH₃)—CH(CH₃)₂ H A-31 (R)CH(CH₃)—CH(CH₃)₂ CH₃ A-32 (R) CH(CH₃)—CH(CH₃)₂ CH₂CH₃ A-33 (S)CH(CH₃)—CH(CH₃)₂ H A-34 (S) CH(CH₃)—CH(CH₃)₂ CH₃ A-35 (S)CH(CH₃)—CH(CH₃)₂ CH₂CH₃ A-36 (R/S) CH(CH₃)—C(CH₃)₃ H A-37 (R/S)CH(CH₃)—C(CH₃)₃ CH₃ A-38 (R/S) CH(CH₃)—C(CH₃)₃ CH₂CH₃ A-39 (R)CH(CH₃)—C(CH₃)₃ H A-40 (R) CH(CH₃)—C(CH₃)₃ CH₃ A-41 (R) CH(CH₃)—C(CH₃)₃CH₂CH₃ A-42 (S) CH(CH₃)—C(CH₃)₃ H A-43 (S) CH(CH₃)—C(CH₃)₃ CH₃ A-44 (S)CH(CH₃)—C(CH₃)₃ CH₂CH₃ A-45 (R/S) CH(CH₃)—CF₃ H A-46 (R/S) CH(CH₃)—CF₃CH₃ A-47 (R/S) CH(CH₃)—CF₃ CH₂CH₃ A-48 (R) CH(CH₃)—CF₃ H A-49 (R)CH(CH₃)—CF₃ CH₃ A-50 (R) CH(CH₃)—CF₃ CH₂CH₃ A-51 (S) CH(CH₃)—CF₃ H A-52(S) CH(CH₃)—CF₃ CH₃ A-53 (S) CH(CH₃)—CF₃ CH₂CH₃ A-54 (R/S) CH(CH₃)—CCl₃H A-55 (R/S) CH(CH₃)—CCl₃ CH₃ A-56 (R/S) CH(CH₃)—CCl₃ CH₂CH₃ A-57 (R)CH(CH₃)—CCl₃ H A-58 (R) CH(CH₃)—CCl₃ CH₃ A-59 (R) CH(CH₃)—CCl₃ CH₂CH₃A-60 (S) CH(CH₃)—CCl₃ H A-61 (S) CH(CH₃)—CCl₃ CH₃ A-62 (S) CH(CH₃)—CCl₃CH₂CH₃ A-63 CH₂C(CH₃)═CH₂ H A-64 CH₂C(CH₃)═CH₂ CH₃ A-65 CH₂C(CH₃)═CH₂CH₂CH₃ A-66 cyclopentyl H A-67 cyclopentyl CH₃ A-68 cyclopentyl CH₂CH₃A-69 —(CH₂)₂CH(CH₃)(CH₂)₂—

The particularly preferred embodiments of the intermediates with respectto the variables correspond to those of the radicals R¹, R², R^(a), R³and X of formula I.

The compounds I are suitable for use as fungicides. They have excellentactivity against a broad spectrum of phytopathogenic fungi, inparticular from the class of the Ascomycetes, Deuteromycetes,Phycomycetes and Basidiomycetes. Some of them have systemic activity andcan be used in crop protection as foliar and soil fungicides.

They are especially important for controlling a large number of fungi ina variety of crop plants such as wheat, rye, barley, oats, rice, maize,grass, bananas, cotton, soybean, coffee, sugar cane, grapevines, fruitspecies, ornamentals and vegetable species such as cucumbers, beans,tomatoes, potatoes and cucurbits, and also in the seeds of these plants.

Specifically, they are suitable for controlling the following plantdiseases:

-   -   Alternaria species, Podosphaera species, Sclerotinia species,        Physalospora canker in vegetables and fruit,    -   Botrytis cinerea (gray-mold) in strawberries, vegetables,        ornamentals and grapevines,    -   Corynespora cassiicola in cucumbers,    -   Colletotrichum species in fruit and vegetables,    -   Diplocarpon rosae in roses,    -   Elsinoe fawcetti and Diaporthe citri in citrus fruits,    -   Sphaerotheca species in cucurbits, strawberries and roses,    -   Cercospora species in groundnuts, sugar beet and eggplants,    -   Erysiphe cichoracearum in cucurbits,    -   Leveillula taurica in bell peppers, tomatoes and eggplants,    -   Mycosphaerella species in apples and Japanese apricot,    -   Phyllactinia kakicola, Gloesporium kaki, in Japanese apricot,    -   Gymnosporangium yamadae, Leptothyrium pomi, Podosphaera        leucotricha and Gloedes pomigena in apples,    -   Cladosporium carpophilum in pears and Japanese apricot,    -   Phomopsis species in pears,    -   Phytophthora species in citrus fruits, potatoes, onions, in        particular Phytophthora infestans in potatoes and tomatoes,    -   Blumeria graminis (powdery mildew) in cereals,    -   Fusarium and Verticillium species in a variety of plants,    -   Glomerella cingulata in tea,    -   Drechslera and Bipolaris species in cereals and rice,    -   Mycosphaerella species in bananas and groundnuts,    -   Plasmopara viticola in grapevines,    -   Personospora species in onions, spinach and chrysanthemums,    -   Phaeoisariopsis vitis and Sphaceloma ampelina in grapefruits,    -   Pseudocercosporella herpotrichoides in wheat and barley,    -   Pseudoperonospora species in hops and cucumbers,    -   Puccinia species and Typhula species in cereals and lawn,    -   Pyricularia oryzae in rice,    -   Rhizoctonia species in cotton, rice and lawn,    -   Stagonospora nodorum and Septoria tritici in wheat,    -   Uncinula necator in grapevines,    -   Ustilago species in cereals and sugar cane, and also    -   Venturia species (scab) in apples and pears.

The compounds I are also suitable for controlling harmful fungi such asPaecilomyces variotii in the protection of materials (for example wood,paper, paint dispersions, fibers or tissues) and in the protection ofstored products.

The compounds I are employed by treating the fungi or the plants, seeds,materials or the soil to be protected against fungal attack with afungicidally effective amount of the active compounds. The applicationcan be carried out before or after the infection of the materials,plants or seeds by the fungi.

The fungicidal compositions generally comprise from 0.1 to 95,preferably from 0.5 to 90, % by weight of active compound.

For use in crop protection, the application rates are, depending on thekind of effect desired, from 0.01 to 2 kg of active compound per ha.

The treatment of seeds generally requires active compound quantities offrom 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram ofseed.

For use in the protection of materials or stored products, the activecompound application rate depends on the kind of application area andeffect desired. Customary application rates in the protection ofmaterials are, for example, from 0.001 g to 2 kg, preferably from 0.005g to 1 kg, of active compound per cubic meter of treated material.

The compounds I can be converted into the customary formulations, e.g.solutions, emulsions, suspensions, dusts, powders, pastes and granules.The use form depends on the specific intended use; in any case, itshould ensure fine and uniform distribution of the compound according tothe invention.

The formulations are prepared in a known manner, e.g. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants, it being possible to use other organicsolvents as auxiliary solvents if water is used as the diluent. Suitableauxiliaries for this purpose are essentially: solvents such as aromatics(e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins(e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones(e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) andwater; carriers such as ground natural minerals (e.g. kaolins, clays,talc, chalk) and ground synthetic minerals (e.g. finely divided silica,silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g.polyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates), and dispersants such as lignosulfite waste liquors andmethylcellulose.

Suitable surfactants are the alkali metal, alkaline earth metal andammonium salts of lignosulfonic acid, naphthalenesulfonic acid,phenolsulfonic acid, and dibutylnaphthalenesulfonic acid,alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcoholsulfates and fatty acids and alkali metal salts and alkaline earth metalsalts thereof, salts of sulfated fatty alcohol glycol ethers,condensation products of sulfonated naphthalene and naphthalenederivatives with formaldehyde, condensation products of naphthalene orof naphthalene sulfonic acid with phenol and formaldehyde,polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol,octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenylpolyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, laurylalcohol polyglycol ether acetal, sorbitol esters, lignosulfite wasteliquors and methylcellulose.

Suitable for preparing directly sprayable solutions, emulsions, pastesor oil dispersions are petroleum fractions having medium to high boilingpoints, such as kerosene or diesel fuel, furthermore coal-tar oils andoils of plant or animal origin, aliphatic, cyclic and aromatichydrocarbons, for example benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof,methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride,cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polarsolvents, for example dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone, and water.

Powders, compositions for broadcasting and dusts can be prepared bymixing or joint grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogenous granules, can be prepared by binding the active compounds tosolid carriers. Solid carriers are, for example, mineral earths, such assilica gel, silicas, silicates, talc, kaolin, atta clay, limestone,lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calciumsulfate, magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, such as ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas and products of vegetable origin, such as cereal meal,tree bark meal, wood meal and nutshell meal, cellulose powders and othersolid carriers.

The formulations generally comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active compound. The activecompounds are employed in a purity of from 90% to 100%, preferably from95% to 100% (according to the NMR spectrum).

Examples of formulations are:

-   -   I. 5 parts by weight of a compound according to the invention        are thoroughly mixed with 95 parts by weight of finely divided        kaolin. This affords a dusting composition comprising 5% by        weight of the active compound.    -   II. 30 parts by weight of a compound according to the invention        are thoroughly mixed with a mixture of 92 parts by weight of        pulverulent silica gel and 8 parts by weight of paraffin oil        which had been sprayed onto the surface of this silica gel. This        affords an active compound preparation having good adhesive        properties (active compound content 23% by weight).    -   III. 10 parts by weight of a compound according to the invention        are dissolved in a mixture comprising 90 parts by weight of        xylene, 6 parts by weight of the addition product of 8 to 10 mol        of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 2        parts by weight of the calcium salt of dodecylbenzenesulfonic        acid and 2 parts by weight of the addition product of 40 mol of        ethylene oxide to 1 mol of castor oil (active compound content        9% by weight).    -   IV. 20 parts by weight of a compound according to the invention        are dissolved in a mixture comprising 60 parts by weight of        cyclohexanone, 30 parts by weight of isobutanol, 5 parts by        weight of the addition product of 7 mol of ethylene oxide to 1        mol of isooctylphenol and 5 parts by weight of the addition        product of 40 mol of ethylene oxide to 1 mol of castor oil        (active compound content 16% by weight).    -   V. 80 parts by weight of a compound according to the invention        are mixed well with 3 parts by weight of the sodium salt of        diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the        sodium salt of a lignosulfonic acid from a sulfite waste liquor        and 7 parts by weight of pulverulent silica gel, and ground in a        hammer mill (active compound content 80% by weight).    -   VI. 90 parts by weight of a compound according to the invention        are mixed with 10 parts by weight of N-methyl-α-pyrrolidone,        affording a solution which is suitable for use in the form of        very small drops (active compound content 90% by weight    -   VII. 20 parts by weight of a compound according to the invention        are dissolved in a mixture comprising 40 parts by weight of        cyclohexanone, 30 parts by weight of isobutanol, 20 parts by        weight of the addition product of 7 mol of ethylene oxide to 1        mol of isooctylphenol and 10 parts by weight of the addition        product of 40 mol of ethylene oxide to 1 mol of castor oil. The        solution is poured into 100 000 parts by weight of water and        finely dispersed therein, affording an aqueous dispersion        comprising 0.02% by weight of active compound.    -   VIII. 20 parts by weight of a compound according to the        invention are mixed well with 3 parts by weight of the sodium        salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by        weight of the sodium salt of a lignosulfonic acid from a sulfite        waste liquor and 60 parts by weight of pulverulent silica gel,        and ground in a hammer mill. The mixture is finely dispersed in        20 000 parts by weight of water, affording a spray liquor        comprising 0.1% by weight of active compound.

The active compounds can be applied as such, in the form of theirformulations or in the application forms prepared therefrom, for examplein the form of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, compositions forbroadcasting, or granules, by spraying, atomizing, dusting, broadcastingor watering. The application forms depend entirely on the intended uses;in any case, they should ensure very fine dispersion of the activecompounds according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (spray powders, oil dispersions) by addition of water.To prepare emulsions, pastes or oil dispersions, the substances can behomogenized in water as such or dissolved in an oil or solvent, by meansof wetting agents, tackifiers, dispersants or emulsifiers. However,concentrates comprising active compound, wetting agent, tackifier,dispersant or emulsifier and possibly solvent or oil which are suitablefor dilution with water can also be prepared.

The active compound concentrations in the ready-to-use preparations canbe varied over a relatively wide range. In general, they are from 0.0001to 10%, preferably from 0.01 to 1%.

It is also possible to use the active compounds with a high degree ofsuccess in the ultra-low-volume (ULV) method, it being possible to applyformulations comprising more than 95% by weight of active compound oreven the active compound without additives.

Oils of various types, herbicides, fungicides, other pesticides andbactericides can be added to the active compounds, if desired evenimmediately prior to application (tank mix). These agents can be addedto the compositions according to the invention in a weight ratio of 1:10to 10:1.

The compositions according to the invention in the use form asfungicides may also be present in combination with other activecompounds, for example with herbicides, insecticides, growth regulators,fungicides or else with fertilizers. In many cases, a mixture of thecompounds I, or of the compositions comprising them, in the use form asfungicides with other fungicides results in a broader fungicidalspectrum of activity.

The following list of fungicides in combination with which the compoundsaccording to the invention can be used is intended to illustrate thepossible combinations, but not to impose any limitations:

-   -   sulfur, dithiocarbamates and their derivatives, such as        iron(III)dimethyldithiocarbamate, zinc dimethyldithiocarbamate,        zinc ethylenebisdithiocarbamate, manganese        ethylenebisdithiocarbamate, manganese zinc        ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide,        ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),        ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc        (N,N′-propylenebisdithiocarbamate),        N,N′-polypropylenebis(thiocarbamoyl)disulfide;    -   nitro derivatives, such as dinitro-(1-methylheptyl)phenyl        crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate,        2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl        5-nitroisophthalate;    -   heterocyclic substances, such as 2-heptadecyl-2-imidazoline        acetate, 2-chloro-N-(4′-chlorobiphenyl-2-yl)nicotinamide,        2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl        phthalimidophosphonothioate,        5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole,        2,3-dicyano-1,4-dithioanthraquinone,        2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl        1-(butylcarbamoyl)-2-benzimidazolecarbamate,        2-methoxycarbonylaminobenzimidazole, 2-(furyl-(2))benzimidazole,        2-(thiazolyl-(4))-benzimidazole,        N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,        N-trichloromethylthiotetrahydrophthalimide,        N-trichloromethylthiophthalimide,    -   N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfuric        diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,        2-thiocyanatomethylthiobenzothiazole,        1,4-dichloro-2,5-dimethoxybenzene,        4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine        2-thio-l-oxide, 8-hydroxyquinoline or its copper salt,        2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,        2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide,        2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,        2-methylfuran-3-carboxanilide,        2,5-dimethylfuran-3-carboxanilide,        2,4,5-trimethylfuran-3-carboxanilide,        N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,        N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,        2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine        2,2,2-trichloroethyl acetal,        piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)formamide,        1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,        2,6-dimethyl-N-tridecylmorpholine or its salts,        2,6-dimethyl-N-cyclododecylmorpholine or its salts,        N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,        N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine,        1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,        1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,        N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolyl urea,        1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone,        1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,        (2RS,        3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole,        α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,        5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,        bis(p-chlorophenyl)-3-pyridinemethanol,        1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,        1,2-bis-(3-methoxycarbonyl-2-thioureido)benzene,    -   strobilurins, such as methyl        E-methoximino-[α-(o-tolyloxy)-o-tolyl]acetate, methyl        E-2-{2-[6-(2-cyanophenoxy)pyridimin-4-yloxy]phenyl}-3-methoxyacrylate,        methyl-E-methoxyimino-[α-(2-phenoxyphenyl)]acetamide,        methyl-E-methoxyimino-[α-(2,5-dimethylphenoxy) tolyl]-acetamide,        methyl        E-2-{2-[2-trifluoromethylpyrid-6-yl]oxymethyl]phenyl}-3-methoxyacrylate,        methyl        (E,E)-methoximino-{2-[1-(3-trifluoromethylphenyl)ethylidene-aminooxymethyl]phenyl}acetate,        methyl        N-(2-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}phenyl)-N-methoxycarbamate,    -   anilinopyrimidines, such as        N-(4,6-dimethylpyrimidin-2-yl)aniline,        N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline,        N-(4-methyl-6-cyclopropylpyrimidin-2-yl)aniline,    -   phenylpyrroles, such as        4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile,    -   cinnamamides, such as        3-(4-chlorophenyl)-3-(3,4-dimethoxy-phenyl)acryloylmorpholide,        3-(4-fluorophenyl)-3-(3,4-dimethoxy-phenyl)acryloylmorpholide,    -   and a variety of fungicides, such as dodecylguanidine acetate,        1-(3-bromo-6-methoxy-2-methylphenyl)-1-(2,3,4-trimethoxy-6-methylphenyl)methanone,        3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide,        hexachlorobenzene, methyl        N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate,        DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)alanine methyl        ester,        N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,        DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,        5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,        3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione,        3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,        N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,        2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide,        1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,        2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzohydryl alcohol,        N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,        1-((bis-(4-fluorophenyl)methylsilyl)-methyl)-1H-1,2,4-triazole,        N,N-dimethyl-5-chloro-2-cyano-4-p-tolylimidazole-1-sulfonamide,        3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide.

SYNTHESIS EXAMPLES

The procedures given in the synthesis examples below were used to obtainfurther compounds I by appropriate modification of the startingmaterials. The compounds obtained in this manner are listed in the tablethat follows, together with physical data.

Example 1 Preparation of5,7-dihydroxy-6-isopropyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine

A mixture of 14 g (0.17 mol) of 3-amino-1,2,4-triazole, 34.3 g (0.17mol) of diethyl 2-isopropylmalonate and 50 ml of tributylamine werestirred at 180° C. for 6 h. The reaction mixture was then cooled to 70°C., an aqueous solution of sodium hydroxide (21 g/200 ml of water) wasadded and the mixture was stirred for 30 min. The organic phase wasseparated and the aqueous phase was extracted with diethyl ether. Theaqueous phase was then acidified using conc. hydrochloric acid and theresulting precipitate was collected by filtration. Drying gave 27 g(0.14 mol) of the title compound.

Example 2 Preparation of5,7-dichloro-6-isopropyl-[1,2,4]-triazolo-[1,5-a]-pyrimidine

A mixture of 25 g (0.13 mol) of5,7-dichloro-6-isopropyl-(1,2,4]-triazolo[1,5-α]-pyrimidine (cf. Ex. 1)and 50 ml of phosphorus oxychloride was refluxed for 8 h. Some of thephosphorus oxychloride was then distilled off, and the residue waspoured into a mixture of methylene chloride and water. The organic phasewas separated off, dried and filtered. The filtrate was freed from thesolvent. This gave 16 g (0.07 mol) of the title compound (melting point119° C.).

Example 3 Preparation of5-chloro-6-isopropyl-7-cyclopentylamino-[1,2,4]-triazolo-[1,5-α]-pyrimidine

With stirring, a mixture of 0.13 g (1.5 mmol) of cyclopentylamine and0.15 g (1.5 mmol) of triethylamine in 10 ml of methylene chloride wasadded to a mixture of 0.34 g (1.5 mmol) of5,7-dichloro-6-isopropyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine (cf. Ex. 2)in 20 ml of methylene chloride. The reaction mixture was stirred at roomtemperature for 16 h and then washed with 5% strength hydrochloric acid.The organic phase was separated off, dried over sodium sulfate andfiltered. The filtrate was freed from the solvent and the residue waspurified chromatographically. This gave 0.32 g (1.14 mmol) of the titlecompound (melting point 139° C.).

Example 4 Preparation of7-hydroxy-6-propyl-5-trifluoromethyl-[1,2,4]-triazolo[1,5-α]-pyrimidine

A mixture of 14 g (0.17 mol) 3-amino-1,2,4-triazole, 38.4 g (0.17 mol)of 3-oxo-2-propyl-4,4,4-trifluorobutanoate and 50 ml of tributylaminewere stirred at 180° C. for 6 h. Work-up was carried out analogously toEx. 1. Drying gave 33 g (0.13 mol) of the title compound.

Example 5 Preparation of7-chloro-6-propyl-5-trifluoromethyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine

A mixture of 25 g (0.10 mol) of5,7-dichloro-6-isopropyl-[1,2,4]-triazolo[1,5-α]-pyrimidine (cf. Ex. 4)and 50 ml of phosphorus oxychloride was heated under reflux for 8 h.Work-up was carried out analogously to Ex. 2. This gave 23 g (0.086 mol)of the title compound (melting point 63° C.).

Example 6 Preparation of7-cyclopentylamino-6-propyl-5-trifluoromethyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine

With stirring, a mixture of 0.13 g (1.5 mmol) of cyclopentylamine and0.15 g (1.5 mmol) of triethylamine in 10 ml of methylene chloride wasadded to a mixture of 0.40 g (1.5 mmol) of7-chloro-6-propyl-5-trifluoromethyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine(cf. Ex. 5) in 20 ml of methylene chloride. The reaction mixture wasstirred at room temperature for 16 h, work-up was carried outanalogously to Ex. 3. This gave 0.39 g (1.24 mmol) of the title compound(melting point 179° C.).

Example 7 Preparation of7-hydroxy-6-octyl-5-phenyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine

A mixture of 14.0 g (0.17 mol) of 3-amino-1,2,4-triazole, 51.7 g (0.17mol) of 3-oxo-2-octyl-4-phenylbutanoate and 3. g of p-toluenesulfonicacid was heated under reflux for 6 h. Work-up was carried outanalogously to Ex. 1. Drying gave 37 g (0.11 mol) of the title compound.

Example 8 Preparation of7-chloro-6-octyl-5-phenyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine

A mixture of 17 g (0.05 mol) of7-hydroxy-6-octyl-5-phenyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine (cf. Ex.7) and 50 ml of phosphorus oxychloride was heated under reflux for 8 h.Work-up was carried out analogously to Ex. 2. This gave 16 g (0.046 mol)of the title compound.

Example 9 Preparation of7-cyclopentylamino-6-octyl-5-phenyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine

With stirring, a mixture of 0.13 g (1.5 mmol) of cyclopentylamine and0.15 g (1.5 mmol) of triethylamine in 10 ml of methylene chloride wasadded to a mixture of 0.52 g (1.5 mmol) of7-chloro-6-octyl-5-phenyl-[1,2,4]-triazolo-[1,5-α]-pyrimidine (cf. Ex.8) in 20 ml of methylene chloride. The reaction mixture was stirred atroom temperature for 16 h, work-up was carried out analogously to Ex. 3.This gave 0.52 g (1.3 mmol) of the title compound (melting point 81°C.).

Example 10 Preparation of5-cyano-6-octyl-7-diethylamino-[1,2,4]-triazolo-[1,5-a]-pyrimidine[I-167]

A mixture of 0.1 mol of the compound I-48 and 0.25 mol oftetraethylammonium cyanide in 750 ml of dimethylformamide was stirred at20-25° C. for about 16 hours. Water and methyl tert-butyl ether wereadded, and the phases were then separated. The organic phase was washedwith water and dried, and the solvent was then removed. The residuegave, after chromatography on silica gel, 8.33 g of the title compound.

¹H-NMR: δ in ppm: 8.5 (s); 3.65 (q); 2.9 (m); 1.7 (m); 1.3 (m); 1.2 (t);0.9 (t).

Example 11 Preparation of5-methoxy-6-octyl-7-diethylamino-[1,2,4]-triazolo-[1,5-α]-pyrimidine[I-168]

At 20-25° C., 71.5 mmol of a 30% strength sodium methoxide solution wereadded to a solution of 65 mmol of the compound I-48 in 400 ml ofanhydrous methanol, and the mixture was then stirred at 20-25° C. forabout 16 hours. The solvent was distilled off and the residue was thentaken up in dichloromethane. This solution was washed with water andthen dried, and the solvent was removed. Chromatography on silica gelgave 7.5 g of the title compound.

¹H-NMR: δ in ppm: 8.18 (s); 4.09 (s); 3.41 (q); 2.65 (m); 1.55 (m); 1.3(m); 1.1 (t); 0.9 (t). TABLE 1 phys. data (m.p. [° C.]; IR[cm⁻¹]; ¹H-NMRδ No. R¹ R² R³ X [ppm] I-1 CH(CH₃)₂ H CH₃ Cl 169 I-2—(CH₂)₂CH(CH₃)(CH₂)₂— CH₃ Cl 125 I-3 cyclopentyl H CH₃ Cl 172 I-4CH₂—CH₃ CH₂—CH₃ CH₃ Cl 96 I-5 CH(CH₃)—CF₃ H CH₃ Cl 209 I-6 CH₂—CF₃ H CH₃Cl 133 I-7 CH₂—C(CH₃)═CH₂ CH₂—CH₃ CH₂—CH₃ Cl 55 I-8 CH(CH₃)₂ CH₂—CH₃ Cl152 I-9 —(CH₂)₂CH(CH₃)(CH₂)₂— CH₂—CH₃ Cl 1543, 1521, 1451 I-10cyclopentyl H CH₂—CH₃ Cl 136 I-11 CH₂—CH₃ CH₂—CH₃ CH₂—CH₃ Cl 1596, 1511,1464 I-12 (CH₂)₂—CH₃ (CH₂)₂—CH₃ CH₂—CH₃ Cl 1595, 1511, 1456 I-13CH—(CH₃)₂ CH₃ CH₂—CH₃ Cl 1593, 1513, 1097 I-14 (R/S)CH(CH₃)—CH₂—CH₃ HCH₂—CH₃ Cl 145 I-15 (R)CH(CH₃)—CH₂—CH₃ H CH₂—CH₃ Cl 140 I-16(S)CH(CH₃)—CH₂—CH₃ H CH₂—CH₃ Cl 140 I-17 (R/S)CH(CH₃)—CH(CH₃)₂ H CH₂—CH₃Cl 119 I-18 (R)CH(CH₃)—CH(CH₃)₂ H CH₂—CH₃ Cl 102 I-19(S)CH(CH₃)—CH(CH₃)₂ H CH₂—CH₃ Cl 102 I-20 (R/S)CH(CH₃)—C(CH₃)₃ H CH₂—CH₃Cl 116 I-21 (R)CH(CH₃)—C(CH₃)₃ H CH₂—CH₃ Cl 1613, 1555, 1464 I-22(S)CH(CH₃)—C(CH₃)₃ H CH₂—CH₃ Cl 1612, 1554, 1464 I-23 (R/S)CH(CH₃)—CF₃ HCH₂—CH₃ Cl 169 I-24 (R)CH(CH₃)—CF₃ H CH₂—CH₃ Cl 140 I-25 (S)CH(CH₃)—CF₃H CH₂—CH₃ Cl 140 I-26 H H CH₂—CH₃ Cl 263 I-27 —(CH₂)₂CH(CH₃)(CH₂)₂—(CH₂)₃—CH₃ Cl 91 I-28 (R/S)CH(CH₃)—CF₃ H (CH₂)₃—CH₃ Cl 125 I-29(R)CH(CH₃)—CF₃ H (CH₂)₃—CH₃ Cl 121 I-30 (S)CH(CH₃)—CF₃ H (CH₂)₃—CH₃ Cl121 I-31 CH₂—CF₃ H (CH₂)₃—CH₃ Cl 156 I-32 CH₂—C(CH₃)═CH₂ H CH₂—CH(CH₃)₂Cl 180 I-33 CH(CH₃)₂ H CH₂—CH(CH₃)₂ Cl 127 I-34 cyclopentyl HCH₂—CH(CH₃)₂ Cl 56 I-35 CH₂CH₃ CH₂CH₃ CH₂—CH(CH₃)₂ Cl 163 I-36CH(CH₃)—CH₂—CH₃ H CH₂—CH(CH₃)₂ Cl 159 I-37 CH(CH₃)₂ HCH(CH₃)—CH₂—CH₂—CH₃ Cl 180 I-38 cyclopentyl H CH(CH₃)—CH₂—CH₂—CH₃ Cl 127I-39 CH₂CH₃ CH₂CH₃ CH(CH₃)—CH₂—CH₂—CH₃ Cl 56 I-40 (R/S)CH(CH₃)—CF₃ HCH(CH₃)—CH₂—CH₂—CH₃ Cl 163 I-41 CH₂—CF₃ H CH(CH₃)—CH₂—CH₂—CH₃ Cl 159I-42 CH(CH₃)₂ H C(CH₃)₃ Cl 136 I-43 —(CH₂)₂CH(CH₃)(CH₂)₂— C(CH₃)₃ Cl 140I-44 CH₂—C(CH₃)═CH₂ CH₂—CH₃ (CH₂)₇—CH₃ Cl 2927, 1597, 1508, 1462 I-45CH(CH₃)₂ H (CH₂)₇—CH₃ Cl 2926, 1613, 1553, 1464 I-46—(CH₂)₂CH(CH₃)(CH₂)₂— (CH₂)₇—CH₃ Cl 2925, 1594, 1520, 1192 I-47cyclopentyl H (CH₂)₇—CH₃ Cl 2927, 1612, 1554, 1059 I-48 CH₂—CH₃ CH₂—CH₃(CH₂)₇—CH₃ Cl 2927, 1598, 1511, 1466 I-49 (CH₂)₂—CH₃ (CH₂)₂—CH₃(CH₂)₇—CH₃ Cl 2927, 1597, 1561, 1457 I-50 CH—(CH₃)₂ CH₃ (CH₂)₇—CH₃ Cl2926, 1595, 1514, 1467 I-51 (R/S)CH(CH₃)—CH(CH₃)₂ H (CH₂)₇—CH₃ Cl 2926,1613, 1553, 1464 I-52 (R)CH(CH₃)—CH(CH₃)₂ H (CH₂)₇—CH₃ Cl 2926, 1612,1553, 1464 I-53 (S)CH(CH₃)—CH(CH₃)₂ H (CH₂)₇—CH₃ Cl 2926, 1612, 1552,1463 I-54 (R/S)CH(CH₃)—C(CH₃)₃ H (CH₂)₇—CH₃ Cl 2926, 1613, 1555, 1464I-55 (R)CH(CH₃)—C(CH₃)₃ H (CH₂)₇—CH₃ Cl 2926, 1613, 1556, 1467 I-56(S)CH(CH₃)—C(CH₃)₃ H (CH₂)₇—CH₃ Cl 2925, 1612, 1556, 1466 I-57(R/S)CH(CH₃)—CF₃ H (CH₂)₇—CH₃ Cl 1619, 1533, 1146 I-58 (R)CH(CH₃)—CF₃ H(CH₂)₇—CH₃ Cl 1620, 1542, 1146 I-59 (S)CH(CH₃)—CF₃ H (CH₂)₇—CH₃ Cl 1619,1541, 1146 I-60 CH₂—C(CH₃)═CH₂ CH₂—CH₃ CH(CH₃)₂ Cl 71 I-61 CH(CH₃)₂ HCH(CH₃)₂ Cl 180 I-62 CH₂—CH₃ CH₂—CH₃ CH(CH₃)₂ Cl 91 I-63 (CH₂)₂—CH₃(CH₂)₂—CH₃ CH(CH₃)₂ Cl 1592, 1506, 1454 I-64 CH—(CH₃)₂ CH₃ CH(CH₃)₂ Cl85 I-65 (R/S)CH(CH₃)—CH₂—CH₃ H CH(CH₃)₂ Cl 1616, 1544, 1463 I-66(R)CH(CH₃)—CH₂—CH₃ H CH(CH₃)₂ Cl 160 I-67 (S)CH(CH₃)—CH₂—CH₃ H CH(CH₃)₂Cl 160 I-68 (R/S)CH(CH₃)—CH(CH₃)₂ H CH(CH₃)₂ Cl 134 I-69(R)CH(CH₃)—CH(CH₃)₂ H CH(CH₃)₂ Cl 120 I-70 (S)CH(CH₃)—CH(CH₃)₂ HCH(CH₃)₂ Cl 120 I-71 (R/S)CH(CH₃)—C(CH₃)₃ H CH(CH₃)₂ Cl 2964, 1611, 1551I-72 (R)CH(CH₃)—C(CH₃)₃ H CH(CH₃)₂ Cl 64 I-73 (S)CH(CH₃)—C(CH₃)₃ HCH(CH₃)₂ Cl 64 I-74 (R/S)CH(CH₃)—CF₃ H CH(CH₃)₂ Cl 1616, 1527, 1147 I-75(R)CH(CH₃)—CF₃ H CH(CH₃)₂ Cl 70 I-76 (S)CH(CH₃)—CF₃ H CH(CH₃)₂ Cl 70I-77 H H CH(CH₃)₂ Cl 271 I-78 CH₂—C(CH₃)═CH₂ CH₂—CH₃ cyclopentyl Cl 66I-79 CH(CH₃)₂ H cyclopentyl Cl 136 I-80 CH₂—CH₃ CH₂—CH₃ cyclopentyl Cl78 I-81 (CH₂)₂—CH₃ (CH₂)₂—CH₃ cyclopentyl Cl 87 I-82 CH₂—C(CH₃)═CH₂CH₂—CH₃ cyclohexyl Cl 136 I-83 CH(CH₃)₂ H cyclohexyl Cl 156 I-84—(CH₂)₂CH(CH₃)(CH₂)₂— cyclohexyl Cl 151 I-85 cyclopentyl H cyclohexyl Cl158 I-86 CH₂—CH₃ CH₂—CH₃ cyclohexyl Cl 103 I-87 (CH₂)₂—CH₃ (CH₂)₂—CH₃cyclohexyl Cl 139 I-88 CH—(CH₃)₂ CH₃ cyclohexyl Cl 134 I-89(R/S)CH(CH₃)—CH₂—CH₃ H cyclohexyl Cl 155 I-90 (R)CH(CH₃)—CH₂—CH₃ Hcyclohexyl Cl 155 I-91 (S)CH(CH₃)—CH₂—CH₃ H cyclohexyl Cl 155 I-92(R/S)CH(CH₃)—CH(CH₃)₂ H cyclohexyl Cl 114 I-93 (R)CH(CH₃)—CH(CH₃)₂ Hcyclohexyl Cl 110 I-94 (S)CH(CH₃)—CH(CH₃)₂ H cyclohexyl Cl 110 I-95(R/S)CH(CH₃)—C(CH₃)₃ H cyclohexyl Cl 134 I-96 (R)CH(CH₃)—C(CH₃)₃ Hcyclohexyl Cl 116 I-97 (S)CH(CH₃)—C(CH₃)₃ H cyclohexyl Cl 116 I-98(R/S)CH(CH₃)—CF₃ H cyclohexyl Cl 160 I-99 (R)CH(CH₃)—CF₃ H cyclohexyl Cl130 I-100 (S)CH(CH₃)—CF₃ H cyclohexyl Cl 130 I-101 CH₂—CF₃ H cyclohexylCl 167 I-102 —(CH₂)₂CH(CH₃)(CH₂)₂— CH₂—C₆H₅ Cl 144 I-103 CH₂—C(CH₃)═CH₂CH₂—CH₃ CH₂-(2-Cl—C₆H₄) Cl 114 I-104 —(CH₂)₂CH(CH₃)(CH₂)₂—CH₂-(2-Cl—C₆H₄) Cl 164 I-105 CH₂—C(CH₃)═CH₂ CH₂—CH₃ CH₂—CH═CH₂ Cl 55I-106 —(CH₂)₂CH(CH₃)(CH₂)₂— CH₂—CH═CH₂ Cl 37 I-107 cyclopentyl HCH₂—CH═CH₂ Cl 43 I-108 (R/S)CH(CH₃)—CF₃ H cyclopropylmethyl Cl 150 I-109CH₂—CF₃ H cyclopropylmethyl Cl 144 I-110 CH(CH₃)₂ H CH₂—CH₂—CN Cl 211I-111 CH₂—C(CH₃)═CH₂ CH₂—CH₃ CH₂—CF₃ Cl 84 I-112 CH(CH₃)₂ H CH₂—CF₃ Cl151 I-113 cyclopentyl H CH₂—CF₃ Cl 163 I-114 CH₂—CH₃ CH₂—CH₃ CH₂—CF₃ Cl103 I-115 (CH₂)₂—CH₃ (CH₂)₂—CH₃ CH₂—CF₃ Cl 107 I-116 CH—(CH₃)₂ CH₃CH₂—CF₃ Cl 88 I-117 (R/S)CH(CH₃)—CH₂—CH₃ H CH₂—CF₃ Cl 131 I-118(R)CH(CH₃)—CH₂—CH₃ H CH₂—CF₃ Cl 126 I-119 (S)CH(CH₃)—CH₂—CH₃ H CH₂—CF₃Cl 126 I-120 (R/S)CH(CH₃)—CH(CH₃)₂ H CH₂—CF₃ Cl 114 I-121(R)CH(CH₃)—CH(CH₃)₂ H CH₂—CF₃ Cl 112 I-122 (S)CH(CH₃)—CH(CH₃)₂ H CH₂—CF₃Cl 112 I-123 (R/S)CH(CH₃)—C(CH₃)₃ H CH₂—CF₃ Cl 110 I-124(R)CH(CH₃)—C(CH₃)₃ H CH₂—CF₃ Cl 105 I-125 (S)CH(CH₃)—C(CH₃)₃ H CH₂—CF₃Cl 105 I-126 (R/S)CH(CH₃)—CF₃ H CH₂—CF₃ Cl 179 I-127 (R)CH(CH₃)—CF₃ HCH₂—CF₃ Cl 125 I-128 (S)CH(CH₃)—CF₃ H CH₂—CF₃ Cl 125 I-129 H H CH₂—CF₃Cl 243 I-130 CH(CH₃)₂ H (CH₂)₇—CH₃ CF₃ 91 I-131 —(CH₂)₂CH(CH₃)(CH₂)₂—(CH₂)₇—CH₃ CF₃ 64 I-132 cyclopentyl H (CH₂)₇—CH₃ CF₃ 84 I-133 H H(CH₂)₇—CH₃ CF₃ 177 I-134 CH(CH₃)₂ H (CH₂)₂—CH₃ CF₃ 162 I-135—(CH₂)₂CH(CH₃)(CH₂)₂— (CH₂)₂—CH₃ CF₃ 108 I-136 (R)CH(CH₃)—C(CH₃)₃ H(CH₂)₂—CH₃ CF₃ 101 I-137 (S)CH(CH₃)—C(CH₃)₃ H (CH₂)₂—CH₃ CF₃ 101 I-138 HH (CH₂)₂—CH₃ CF₃ 241 I-139 CH(CH₃)₂ H (CH₂)₇—CH₃ C₆H₅ 83 I-140—(CH₂)₂CH(CH₃)(CH₂)₂— (CH₂)₇—CH₃ C₆H₅ 63 I-141 H H (CH₂)₇—CH₃ C₆H₅ 163I-142 —(CH₂)₂CH(CH₃)(CH₂)₂— cyclopentyl Cl 2960, 1610, 1550, 1241 I-143cyclopentyl H cyclopentyl Cl 154 I-144 CH—(CH₃)₂ CH₃ cyclopentyl Cl2958, 1610, 1548, 1239 I-145 (R/S)CH(CH₃)—CH₂—CH₃ H cyclopentyl Cl 143I-146 (S)CH(CH₃)—CH₂—CH₃ H cyclopentyl Cl 137 I-147 (R)CH(CH₃)—CH₂—CH₃ Hcyclopentyl Cl 137 I-148 (R/S)CH(CH₃)—CH(CH₃)₂ H cyclopentyl Cl 124I-149 (S)CH(CH₃)—CH(CH₃)₂ H cyclopentyl Cl 110 I-150 (R)CH(CH₃)—CH(CH₃)₂H cyclopentyl Cl 110 I-151 (R/S)CH(CH₃)—C(CH₃)₃ H Cyclopentyl Cl 113I-152 (S)CH(CH₃)—C(CH₃)₃ H cyclopentyl Cl 2962, 1610, 1550, 1241 I-153(R)CH(CH₃)—C(CH₃)₃ H cyclopentyl Cl 2960, 1610, 1549, 1241 I-154(R/S)CH(CH₃)—CF₃ H cyclopentyl Cl 129 I-155 (S)CH(CH₃)—CF₃ H cyclopentylCl 135 I-156 (R)CH(CH₃)—CF₃ H cyclopentyl Cl 135 I-157 H HCH(CH₃)—(CH₂)₅—CH₃ CF₃ 129 I-158 H H (CH₂)₃—CH(CH₃)₂ CF₃ 213 I-159 H H(CH₂)₆—CH₃ CF₃ 180 I-160 H H (CH₂)₅—CH₃ CF₃ 208 I-161 H HCH(CH₂CH₃)—(CH₂)₃—CH₃ CF₃ 162 I-162 H H CH(CH₂CH₂CH₃)₂ CF₃ 164 I-163 H HCH(CH₃)—(CH₂)₃—CH₃ CF₃ 148 I-164 H H (CH₂)₇—CH₃ Cl 277 I-165 H Hcyclopentyl Cl 8.4(s); 8.2(m); 3.45(m); 1.95(m); 1.8(m); 1.6(m) I-166 HH cyclohexyl Cl 8.45(s); 8.2(m); 3.1(m); 2.1(m); 1.8(m); 1.55(m); 1.4(m)I-167 CH₂—CH₃ CH₂—CH₃ (CH₂)₇—CH₃ CN see example 10 I-168 CH₂—CH₃ CH₂—CH₃(CH₂)₇—CH₃ OCH₃ see example 11

Examples of the Action Against Harmful Fungi

The fungicidal action of the compounds of the formula I was demonstratedby the following tests:

The active compounds were prepared separately or jointly as a 10%strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% byweight of NekanilR [sic] .LN (Lutensol® AP6, wetting agent havingemulsifying and dispersing action based on ethoxylated alkylphenols) and10% by weight of WettolR [sic] EM (nonionic emulsifier based onethoxylated castor oil) and diluted with water to the desiredconcentration.

Use Example 1 Activity Against Botrytis cinerea on Bell Pepper Leaves

Bell pepper seedlings of the cultivar “Neusiedler Ideal Elite” were,after 4-5 leaves were well-developed, sprayed to runoff point with anaqueous preparation of active compound which had been prepared from astock solution of 10% of active compound, 85% of cyclohexanone and 5% ofemulsifier. The next day, the treated plants were inoculated with aspore suspension of Botrytis cinerea which contained 1.7×10⁶ spores/mlin a 2% strength aqueous biomalt solution. The test plants were thenplaced in a climatized chamber at 22-24° C. and high atmospherichumidity. After 5 days, the extent of the fungal attack on the leavescould be determined visually in %.

In this test, the [lacuna] with 250 ppm of active compounds I-10, I-61,I-65, I-66, I-68, I-69, I-76, I-78, I-84, I-100, I-101, I-146 and I-153to I-155 showed no or at most 15% infection, whereas the untreatedplants were 90% infected.

Use Example 2 Activity Against Downy Mildew on Grapevines (Plasmoparaviticola)

Leaves of potted vines of the cultivar “Müller-Thurgau” were sprayed torunoff point with an aqueous preparation of active compound which hadbeen prepared from a stock solution of 10% of active compound, 85% ofcyclohexanone and 5% of emulsifier. The next day, the leaves wereinoculated with an aqueous zoospore suspension of Plasmopara viticola.The grapevines were initially placed in a water-vapor-saturated chamberat 24° C. for 48 hours and then in a greenhouse at 20-30° C. for 5 days.After this period of time, the plants were once more placed into a moistchamber for 16 hours to promote sporangiophore eruption. The extent ofthe development of the infection on the undersides of the leaves wasthen determined visually.

In this test, the [lacuna] with 250 ppm of active compounds I-8 to I-10,I-19, I-25, I-27, I-49, I-60 to I-62, I-69, I-84, I-101, I-113, I-133,I-146 and I-153 to I-155 showed no or at most 15% infection, whereas theuntreated plants were 85% infected.

1. A 7-aminotriazolopyrimidine of the formula I,

where: R¹, R² are hydrogen, C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, C₃-C₈-cycloalkyl, phenyl, naphthyl; or 5- or 6-memberedheterocyclyl containing one to four nitrogen atoms or one to threenitrogen atoms and one sulfur or oxygen atom; or 5- or 6-memberedheteroaryl containing one to four nitrogen atoms or one to threenitrogen atoms and one sulfur or oxygen atom, where R¹ and R²,independently of one another, may, if they are not hydrogen, bepartially or fully halogenated and/or may carry one to three radicalsfrom the group R^(a) R^(a) is cyano, nitro, hydroxyl, C₁-C₆-alkyl,C_(l)-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyl,C₂-C₆-alkenyloxy, C₂-C₆-alkynyl, C₃-C₆-alkynyloxy and unhalogenated orhalogenated oxy-C₁-C₄-alkyleneoxy; or R¹ and R² together with thelinking nitrogen atom may form a 5- or 6-membered ring which containsone to four nitrogen atoms or one to three nitrogen atoms and one sulfuror oxygen atom and which may be substituted by one to three radicalsfrom the group R^(a); R³ is C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl-, C₃-C₈-cycloalkyl, phenyl-C₁-C₁₀-alkyl, where R³ may beunsubstituted or partially or fully halogenated and/or may carry one tothree radicals from the group R^(a), or C₁-C₁₀-haloalkyl which may carryone to three radicals from the group R^(a); X is halogen, cyano,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, phenyl or R^(a)-substituted phenyl; andits salts.
 2. A 7-aminotriazolopyrimidine of the formula I as claimed inclaim 1 in which X is halogen.
 3. A process for preparing7-aminotriazolopyrimidines of the formula I as claimed in claim 1 inwhich X is halogen, cyano or C₁-C₄-alkoxy, which comprises cyclizingdicarbonyl compounds of the formula II.1,

where A¹ and A² are C₁-C₁₀-alkoxy, with 3-amino-1,2,4-triazole of theformula III

to give hydroxytriazolopyrimidines of the formula IV.1

halogenating the hydroxytriazolopyrimidines of the formula IV.1 with ahalogenating agent to give halotriazolopyrimidines of the formula V.1

where Hal is halogen, followed by reaction with an amine of the formulaVI

to give 7-aminotriazolopyrimidines of the formula I in which X ishalogen, and, to prepare 7-aminotriazolopyrimidines of the formula I inwhich X is cyano or C₁-C₄-alkoxy, reacting with a compound of theformula VIIM-X′  VII in which M is an ammonium, tetraalkylammonium, alkali metal oralkaline earth metal cation and X′ is cyano or alkoxy.
 4. A process forpreparing compounds of the formula I as claimed in claim 1, in which Xis C₁-C₄-haloalkyl or unsubstituted or R^(a)-substituted phenyl, whichcomprises cyclizing dicarbonyl compounds of the formula II.2

where A¹ is C₁-C₁₀-alkoxy and X is C₁-C₄-haloalkyl or unsubstituted orR^(a)-substituted phenyl with 3-amino-1,2,4-triazole of the formula IIIas claimed in claim 3 to give 7-hydroxytriazolopyrimidines of theformula IV.2

halogenating the 7-hydroxytriazolopyrimidines of the formula IV.2 with ahalogenating agent to give 7-halotriazolopyrimidines of the formula V.2

where Hal is halogen, followed by reaction with an amine of the formulaVI as claimed in claim 3 to give 7-aminotriazolopyrimidines of theformula I.
 5. A composition suitable for controlling harmful fungi,which comprises a solid or liquid carrier and a7-aminotriazolopyrimidine of the formula I as claimed in claim
 1. 6. Theuse of the 7-aminotriazolopyrimidines of the formula I as claimed inclaim 1 for preparing a composition suitable for controlling harmfulfungi.
 7. A method for controlling harmful fungi, which comprisestreating the fungi or the materials, plants, the soil or the seeds to beprotected against fungal attack with an effective amount of the7-aminotriazolopyrimidines of the formula I as claimed in claim 1.